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Structure of 75-98-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only !
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Qing Yun Li ; Leigh Anna Hunt ; Kalpani Hirunika Wijesinghe ; Christine Curiac ; Ashley Williams ; Amala Dass , et al.
Abstract: Strong photoinduced oxidants are important to organic synthesis and solar energy conversion, to chemical fuels or electric. For these applications, visible light absorption is important to solar energy conversion and long-lived excited states are needed to drive catalysis. With respect to these desirable qualities, a series of five 5,6-dicyano[2,1,3]benzothiadiazole (DCBT) dyes are examined as organic chromophores that can serve as strong photooxidants in catalytic systems. The series utilizes a DCBT core with aryl groups on the periphery with varying electron donation strengths relative to the core. The dyes are studied via both steady-state and transient absorption and emission studies. Additionally, computational analysis, voltammetry, crystallography, and absorption spectroelectrochemistry are also used to better understand the behavior of these dyes. Ultimately, a strong photooxidant is arrived at with an exceptionally long excited state lifetime for an organic chromophore of 16 µs. The long-lived excited state photosensitizer is well-suited for use in catalysis, and visible light driven photosensitized water oxidation is demonstrated using a water-soluble photosensitizer.
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Purchased from AmBeed: 54512-79-7 ; 5798-75-4 ; 328-70-1 ; 586-76-5 ; 22385-77-9 ; 3109-63-5 ; 23783-42-8 ; 3375-31-3 ; 1122-58-3 ; 479094-62-7 ; 75-98-9 ; 51364-51-3 ; 538-75-0 ; 584-08-7 ; 1122-91-4 ; 123-30-8 ; 108-88-3 ; 109-77-3 ; 64-19-7 ; 603-35-0
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CAS No. : | 75-98-9 |
Formula : | C5H10O2 |
M.W : | 102.13 |
SMILES Code : | CC(C)(C)C(O)=O |
MDL No. : | MFCD00004194 |
InChI Key : | IUGYQRQAERSCNH-UHFFFAOYSA-N |
Pubchem ID : | 6417 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302+H312-H314 |
Precautionary Statements: | P280-P303+P361+P353-P304+P340-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 3265 |
Packing Group: | Ⅱ |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.8 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 27.66 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.28 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.47 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.12 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.89 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.2 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.99 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.33 |
Solubility | 4.74 mg/ml ; 0.0464 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.86 |
Solubility | 1.41 mg/ml ; 0.0138 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.39 |
Solubility | 41.8 mg/ml ; 0.409 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.88 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.0 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | Stage #1: With ammonium peroxydisulfate; sulfuric acid; silver nitrate In water at 70℃; for 1 h; |
Synthesis of Compound J.1. A flask was charged with 3,6-dichloropyridazine (1.49 g, 0.01 mol, 1.0 equiv), silver nitrate (0.17 g, 0.001 mol, 0.1 equiv), water (30 mL), pivalic acid (3.57 g, 0.035 mol, 3.5 equiv), and sulfuric acid (1.6 mL, 0.03 mol, 3.0 equiv). The mixture was heated to 70° C. and a solution of ammonium persulfate (2.28 g, 0.01 mol, 1.0 equiv) in water (10 mL) was added dropwise over ten minutes. The reaction was stirred at 70° C. for one hour and then cooled to RT. The reaction mixture was poured into ice water and then adjusted to pH 8 with aqueous ammonium hydroxide. The aqueous mixture was extracted with CH2Cl2 (2.x.250 mL). The combined organic extracts were filtered through a cotton plug, washed with aqueous 1 N NaOH (70 mL), dried over anhydrous MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography (20percent EtOAc/hexanes) afforded the title compound (1.32 g, 64percent) as a white solid. 1H NMR: (CDCl3, 400 MHz) δ: 7.5 (s, 1H), 1.5 (s, 9H); Rf=0.5 (80percent EtOAc/hexanes). |
64% | With ammonium peroxydisulfate; sulfuric acid; silver nitrate In water at 70℃; for 1 h; | A flask was charged with 3,6-dichloropyridazine (1.49 g, 0.01 mol, 1.0 equiv), silver nitrate (0.17 g, 0.001 mol, 0.1 equiv), water (30 mL), pivalic acid (3.57 g, 0.035 mol, 3.5 equiv), and sulfuric acid (1.6 mL, 0.03 mol, 3.0 equiv). The mixture was heated to 70° C. and a solution of ammonium persulfate (2.28 g, 0.01 mol, 1.0 equiv) in water (10 mL) was added dropwise over ten minutes. The reaction was stirred at 70° C. for one hr and then cooled to RT. The reaction mixture was poured into ice water and then adjusted to pH 8 with aqueous ammonium hydroxide. The aqueous mixture was extracted with CH2Cl2 (2.x.250 mL). The combined organic extracts were filtered through a cotton plug, washed with aqueous 1 N NaOH (70 mL), dried over anhydrous MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography (20percent EtOAc/hexanes) afforded the title compound (1.32 g, 64percent) as a white solid. 1H NMR: (CDCl3, 400 MHz) δ: 7.5 (s, 1 H), 1.5 (s, 9 H); Rf=0.5 (80percent EtOAc/hexanes). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With silver nitrate In hexane; water | a 3,6-Dichloro-4-(1,1-dimethylethyl)pyridazine Concentrated sulphuric acid (53.6 ml, 1.0 mol) was added carefully to a stirred suspension of 3,6-dichloropyridazine (50.0 g, 0.34 mol) in water (1.25 l). This mixture was then heated to 70° C. (internal temperature) before the addition of trimethylacetic acid (47.5 ml, 0.41 mol). A solution of silver nitrate (11.4 g, 0.07 mol) in water (20 ml) was then added over approximately one minute. This caused the reaction mixture to become milky in appearance. A solution of ammonium persulphate (230 g, 1.0 mol) in water (0.63 l) was then added over 20-30 minutes. The internal temperature rose to approximately 85° C. During the addition the product formed as a sticky precipitate. Upon complete addition the reaction was stirred for an additional 10 minutes, then allowed to cool to room temperature. The mixture was then poured onto ice and basified with concentrated aqueous ammonia, with the addition of more ice as required to keep the temperature below 10° C. The aqueous was extracted with dichloromethane (3*300 ml). The combined extracts were dried (MgSO4), filtered and evaporated to give 55.8 g of crude product as an oil. This was purified by silica gel chromatography using 0-15percent ethyl acetate in hexane as eluent to give 37.31 g (53percent) of the desired compound. Data for the title compound: 1H NMR (360 MHz, d6-DMSO) δ1.50 (9H, s), 7.48 (1H, s); MS (ES+) m/e 205 [MH]+, 207 [MH]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium persulfate; aq. sulfuric acid; silver nitrate; | (a) Ethyl 6-(tert-butyl)-2-methylpyridine-3-carboxylate. Analogous to the procedure used to prepare Example 44, step (a), <strong>[1721-26-2]ethyl 2-methylnicotinate</strong> (8.3 g, 50 mmol, Aldrich), trimethylacetic acid (26 g, 250 mmol, Aldrich), silver nitrate (1.7 g, 10 mmol, Aldrich), 10percent aq. sulfuric acid (50 mL) and ammonium persulfate (23 g, 100 mmol, Aldrich) provided, after purification by silica gel chromatography (80:20 hexane:EtOAc), the title product. MS (ESI, pos. ion) m/z: 222 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
200 mg | With trichlorophosphate; for 4h;Reflux; | Example 8 1- (2-tert-Butyl-l-methyl-lH-benzimidazol-6-yl) -4- ( (4- fluorobenzyl) oxy) pyridin-2 (1H) -one A) 6-Bromo-2-tert-butyl-l-methyl-lH-benzimidazole To a. stirred solution of 2 , 2-dimethylpropionic acid (304 mg) and 4-bromo-N2-methylbenzene-l, 2-diamine (400 mg) was added P0C13 (5 ml) , and the mixture was heated at reflux for 4 h. The mixture was then cooled to room temperature, and poured into ice-cold saturated NaHC03 solution. The mixture was extracted with EtOAc, and the organic layer was washed with brine, dried over Na2SC>4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (200 mg) as a light orange solid. MS (ESI+) : [M+H]+ 266.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.2% | 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (47.7 g, 148.69 mmol) was added portionwise over 15 minutes to a stirred suspension of N-ethyl-N-isopropylpropan-2-amine (70.6 mL, 405.51 mmol), pivalic acid (17.08 mL, 148.69 mmol) and <strong>[6761-52-0]3-aminopyrazine-2-carbohydrazide</strong> (20.7 g, 135.17 mmol) in acetonitrile (350 mL) and the reaction mixture was stirred at 80 C. for 20 minutes (a solution was obtained). The reaction mixture was cooled to 0 C. and N-ethyl-N-isopropylpropan-2-amine (70.6 mL, 405.51 mmol), followed by 4-methylbenzene-1-sulfonyl chloride (77 g, 405.51 mmol) were added over a period of 15 minutes. The reaction mixture (yellow suspension) was brought to reflux (solubilisation) and then allowed to stir at room temperature for 14 hours affording a dark orange solution. The solution was concentrated. The residue was diluted with dichloromethane, washed with water, brine, dried over magnesium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 40% ethyl acetate in dichloromethane. The solvent was evaporated to dryness. The resulting mixture was triturated with ether (100 mL), filtered, washed with the minimum of ether and dried to afford 3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (20.8 g, 70.2%) as a pale yellow soild: 1H NMR Spectrum; (CDCl3) 1.53 (9H, s), 1.58-1.68 (2H, m), 6.67 (2H, s), 8.13 (2H, dt); Mass Spectrum [M+H]+=220. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.8 g | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 - 100℃; | 3.10.2 Preparation of ethyl 5-(tert-butyl)-1,2,4-oxadiazole-3-carboxylate (949-4) To a stirred solution of ethyl 2-(hydroxyamino)-2-iminoacetate (5.0 g, 37.8 mmol) in DMF (60 mL) were added pivalic acid (3.86 g, 37.8 mmol), 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI) (7.97 g, 41.58 mmol), HOBt (6.12 g, 45.3 mmol) and DIPEA (19.7 mL, 113.4 mmol). After being stirred at room temperature overnight, the reaction mixture was heated up to 100 C. for hr before cooled down to room temperature and partitioned between EA and H2O. The layers were separated and the aqueous layer was extracted with EA (3*). The combined organic layers were washed with brine and dried over Na2SO4. The solvents were removed and the residue was purified by flash chromatography (silica gel, 10?90% ethyl acetate in petroleum ether) to provide ethyl 5-(tert-butyl)-1,2,4-oxadiazole-3-carboxylate (949-4) (1.8 g, 24%) as a yellow solid. LC-MS: ESI m/z (M+1)=199.36. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.71% | With ammonium peroxydisulfate; sulfuric acid; silver nitrate; In water; at 75℃; for 0.5h;Inert atmosphere; | A solution of 2, 2-dimethylpropanoic acid (4.91 mL, 42.8 mmol) and silver nitrate (1.45 g, 8.56 mmol) in a mixture of sulfuric acid (5.43 mL, 102 mmol) in water (180 mL) was degassed and purged with nitrogen for 3 times. Ethyl lH-imidazole-2-carboxylate (2.00 g, 14.3 mmol) was added to the mixture. A solution of ammonium persulfate (9.77 g, 42.8 mmol) in water (50 mL) was added to the mixture. The reaction mixture was stirred at 75 °C for 30 min under nitrogen. The reaction was terminated by pouring it onto ice. The resulting mixture was made alkaline with 30percent ammonium hydroxide solution (200 mL), and extracted with DCM (200 mL x 3). The combined extracts were washed with brine (300 mL), stirred with saturated aqueous sodium sulfite (300 mL) for 30 min. The layers were separated, and the organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue. The residue was purified by silica gel chromatography (eluting gradient: petroleum ether : ethyl acetate = 20: 1 to 0: 1). Ethyl 4- tert-butyl-lH-imidazole-2-carboxylate (200 mg, 5.71percent yield) was obtained as a yellow oil. LCMS (ESI): m/z = 197.1 [M+H]+. |
Tags: 75-98-9 synthesis path| 75-98-9 SDS| 75-98-9 COA| 75-98-9 purity| 75-98-9 application| 75-98-9 NMR| 75-98-9 COA| 75-98-9 structure
A240989 [143174-36-1]
Sodium Trimethylacetate xHydrate
Similarity: 0.94
A128522 [4835-90-9]
3-Hydroxy-2,2-dimethylpropanoic acid
Similarity: 0.89
A128522 [4835-90-9]
3-Hydroxy-2,2-dimethylpropanoic acid
Similarity: 0.89
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P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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